Dimethylformamide → 3-Chloro-2-methyl-6-nitrobenzonitrile

HRID 322006

Reaktionsgleichung

Reaktionsgleichung von HRID 322006
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12].[C:13]([Cu])#[N:14].CN(C=O)C>C(OCC)(=O)C>[Cl:11][C:4]1[C:3]([CH3:12])=[C:2]([C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)[C:13]#[N:14]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 971552,6-Dichloro-3-nitrotolueneHCID 178418546HCID 178418546, Verbindung2×

Produkt 1

HCID 220089613-Chloro-2-methyl-6-nitrobenzonitrileAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 10 g (49 mmol) of 2,6-dichloro-3-nitrotoluene and 4.8 g (54.0 mmol) of CuCN in 100 ml of abs. DMF was stirred at 150° C. for 6 h, a further 2.4 g (27.0 mmol) of CuCN being added after 4 h. The solvent was stripped off and the residue obtained taken up in ethyl acetate. The precipitate deposited was filtered off and extracted several times with warm ethyl acetate. The combined ethyl acetate solutions were washed with H2O, dilute ammonia solution, and saturated NaCl solution, dried over Na2SO4, and concentrated to dryness. The resulting yellow, crystalline residue was purified by column chromatography on SiO2 using EA/n-heptane 1:10 as a solvent. 5.8 g of the title compound resulted in the form of yellow crystals.

Aufarbeitung

  1. customthe residue obtained
  2. filtrationThe precipitate deposited was filtered off
  3. extractionextracted several times with warm ethyl acetate
  4. washThe combined ethyl acetate solutions were washed with H2O, dilute ammonia solution, and saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe resulting yellow, crystalline residue was purified by column chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-dee4e1ef582640dcb0215f4430dde985
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211196B1

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